
Holiday Homes in Hillsborough County
Find and book unique holiday homes on Airbnb
Top-rated Holiday Homes in Hillsborough County
Guests agree: These holiday homes are highly rated for location, cleanliness and more.

FREE Decor AnyOccasion*Romantic Getaway*Relax Bath
A modern & cozy place in Tampa,private entrance and parking.We include decorations for all occasions:birthday,wedding,special day, show your love, and more!Perfect romantic getaway to enjoy with your loved one.Located in a central area of Tampa,close to Bush Garden/Adventure Island,Raymond James Stadium,Tampa International Airport, Ybor City, Downtown Tampa,Amalie Arena,River Walk,Clearwater/St Pete Beach and more! Peaceful and centrally-located place with very good restaurants and many shops.

#17 New Executive King Bed Home - Joyful Moment
Leave the stress of everyday life behind and head to this 2-bedroom, 2-bathroom home in Tampa. This well-appointed vacation rental has enough room for your group and is conveniently located near plenty of family-friendly activities. At this home, you’ll also be far enough from downtown that you can relax, but close enough to take advantage of all of the professional sports games, museums, and parks that the city offers. After a day out enjoy the backyard and the Beautiful Lake. pictures to come

Modern Home Great Location
Welcome to your home away from home. Our guests’ comfort is our priority. Equipped with all your creature comforts and surrounded by modern fixtures and decor to ensure a wonderful vacation. Open Floor plan, huge kitchen, and two cozy bedrooms. Walking distance to all the local restaurants and attractions, without the noise to keep you up at night; you couldn't choose a better location Please note: this is a duplex property, so you'll be sharing the building but enjoying your own private space.

Sun & Salt Air House-3BR home w/patio,pool,firepit
The search for the perfect sunset with friends and family is over. Minutes from one of a kind shopping, diverse dining, horse racing, and hiking. There is something for everyone. Home is completely renovated with gorgeous stone floors, chef kitchen, and custom outdoor space. Watch the Game on the 75" TV, or relax on the oversized patio/pool area. Enjoy the picturesque sunset before taking an evening dip in the LED lit salt water pool while staying warm by the gas firepit with loved ones.

Villa Al Golfo Three Pristine Waterfront Oasis
Pristine villa in the lovely seaside gulf town of Indian Rocks Beach, 2 short blocks to the beach with intracoastal waters in the backyard. All newly renovated, both inside and out, enjoy unobstructed water views, private entrance, personal patio and your own show stopping indoor/outdoor fireplace. When you aren't lounging outside or taking a glide on our paddle board, you'll love the gourmet kitchen, comfy living room, two large TV's, cable/wifi, luxe memory foam beds & security safe.

Stunning Waterfront Condo at Boca Ciega Resort 310
Do you want to watch dolphins from your balcony? Our condo is beautiful right on the water with a boho style interior design. Large balcony with stunning view over Boca Ciega Bay. Dolphins come in every evening. 4 people easily sleep here, two in the King size bed in the bedroom, and 2 in the $1,600.00 queen size sofa bed in the living room. Fully equipped bar kitchen. There are 2 TVs, Wi-Fi, and washing machine with dryer. Private parking. The condo is smoke free and pet friendly!

Serene Waterfront Townhome at Little Harbor
Come enjoy yourself at our townhome. Relax with the whole family at this peaceful place to stay with four private balconies. Our townhome is located in the seaside village of Little Harbor with a white sand secluded beach, two waterfront restaurants, seaside pool, tennis courts, fishing piers, watersports rentals, two onsite marinas, and much more. Enjoy watching the fish jump and the many varieties of birds in the natural preserve framed by the canal from your private balconies.

Bright & Breezy Tropical Home Minutes to Beach
Relax & Recharge in a Stylish Mid-Century Tropical Getaway – Just Minutes from the Beach! 2BR/2BA with a bonus bedroom in the Florida room—sleeps up to 8. Nestled in a quiet neighborhood just minutes from Indian Rocks and Clearwater Beach, with great dining and shopping. Enjoy a private fenced backyard and BBQ area. Perfect for families or groups seeking comfort and convenience. Pet-Friendly! One well-behaved dog is welcome (an additional $225 pet fee applies). Sorry, no cats.

4-bedroom Vacation home with heated pool family
🎊🎉🎊🎉A new surprise for you, the house has been completely renovated .2025 🎉🎊🎉🎊Bring the whole family to this great place with lots of room for fun. Fishing lake. Free one bottles of wine. **Near Amenities:*** Our location is very convenient, just a short distance from key tourist attractions and local shops. You can easily explore local culture and enjoy new experiences. Contact us to book now and experience our comfortable and warm space!

Reinel’s private apartment in Tampa
Close to the Tampa Zoo,Bush Gardens,adventure Island, and more ————————————————————— St Joseph’s hospital 7 minutes away ————————————————————— Multiple malls close ————————————————————— 10 Minutes away from Downtown Tampa ————————————————————— Tampa International airport 10 minutes away ————————————————————— Raymond James stadium 8 minutes away ————————————————————— ⭐️ ⭐️ ⭐️ ⭐️ ⭐️

Maximalist space w/eclectic style/Bars close by
Welcome to my little slice of paradise! This sunny 2-bedroom retreat sits on the top floor of a charming Floridian townhouse, right in the heart of trendy Seminole Heights. Just a short stroll or bike ride to buzzing cafes, cool bars, local breweries, and foodie hotspots—Tampa’s tastiest treasures are all around you! Whether you're here with family or friends, you're in for a fun-filled stay packed with flavor, flair, and good vibes.

Mango Tango Cottage. Renovated September2025
Escape to our sun-soaked 1-bed, 1-bath studio tucked in a 9-cottage tropical oasis on quiet Cyprus Ave. Steps from Chapel by the Sea, this lush garden hideaway boasts swaying palms, two heated pools and a two-minute stroll to Clearwater Beach. Inside, enjoy crisp modern décor, bright accents and turquoise touches that echo the sea. Peaceful and private, yet close to shops and restaurants, it’s spotless and a cozy retreat for two
Popular amenities for Hillsborough County holiday homes
Family-Friendly holiday homes

Renovated 2 bed/1 bath North End, beach 2 min walk

Modern Home Great Location

Reinel’s private apartment in Tampa

Maximalist space w/eclectic style/Bars close by

Beautiful Clearwater home!

Sun & Salt Air House-3BR home w/patio,pool,firepit

Villa Al Golfo Three Pristine Waterfront Oasis

FREE Decor AnyOccasion*Romantic Getaway*Relax Bath
Holiday home rentals with a patio

Lovely one bedroom, Private Bungalow

Lovely 1 bedroom, unique outdoor space, near park

Beach Condo - Ram Sea - 3BR Condo right on Beach

GK Oasis 2 King BR Dock Kayaks Canal Pool Spa ;Pet

Serene Waterfront Oasis • Kayaks + Dock + Wildlife

Stylish 2 Bedroom Beach Retreat

Gulf Coast Beachfront Paradise

Lovely Efficiency with Patio near Beach
Holiday home rentals with a washing machine and dryer

Central Florida Vacation Stilt Home with pool!

Waterfront Seaside Oasis! Dog-Friendly, pool & spa

Waterfront Escape: 5Bed, 3Bath, Heated Pool!

Modern 4 BR Heated Pool House w Theater Game Room

Sunrise Escape waterfront - pool heater avail

*Updated House* 3 minutes to Beach Access

Brand new vacation rental one block from the beach

Centric Vacation Home with Tiny House near Beaches
Destinations to explore
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- Holiday home rentals Florida
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- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Reunion Resort Golf Courses - Palmer & Watson
- Weeki Wachee Springs
- Coquina Beach
- Vinoy Park
- Dunedin Beach
- Lido Key Beach
- Amalie Arena
- Cortez Beach
- Bean Point Beach
- Island H2O Live!
- Anna Maria Public Beach
- Jannus Live
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- Tampa Palms Golf & Country Club
- ZooTampa at Lowry Park
- River Strand Golf and Country Club
- Hard Rock Casino
- North Beach At Fort DeSoto Park
- Bok Tower Gardens
- Things to do Hillsborough County
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- Things to do Florida
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